Preparation of ( S)-2-substituted succinates by stereospecific reductions of fumarate and derivatives with resting cells of Clostridium formicoaceticum

Abstract

Fumarate derivatives have been reduced to ( S)-2-methylsuccinate 2a, ( S)-2-ethylsuccinate 3a and ( S)-2-chlorosuccinate 4a in up to 1 M concentrations with Clostridium formicoaceticum. Formate was the electron donor and viologens or anthraquinone-2,6-disulphonate acted as artificial electron mediators. Reductions with freeze-dried cells in 2H 2O-buffers led to the (2 R,3 S)-[2,3-2, 2H]-dideuterated succinate derivatives. The productivity numbers 1 ranged from 450 to 5000 and the enantiomeric excess of all ( S)-2-substituted succinates was ⩾99 %.